Bioactive compounds

ABSTRACT

Novel bioactive compounds which when applied to plants in bioregulatory amounts, enhance plant development responses, resulting in enhanced plant properties such as increased total biomass, increased yield, and increased plant quality. Some of the compounds increase the content of taxol and related taxanes in yew plants. One compound, 2- diethylaminoethyl!-2-methylpropylether causes plants treated with the compound to have resistance to chewing insects. The compound 2- diethylaminoethyl!-2-methyl-2-phenylpropylether causes plants treated with the compound to have resistance to sucking insects.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to and has among its objects the provisionof novel bioactive compounds. In one aspect of the invention, thecompounds are plant biochemical regulators which are useful forenhancing plant growth including increasing total plant biomass andimportant plant constituents thereby increasing crop yield and plantquality. In another aspect, selected compounds are useful to increasethe content of taxol and related taxanes in yew plants. In anotheraspect, selected compounds are useful to elicit resistance in plants tosucking or chewing insects.

2. Description of the Art

Advancements in agriculture have led to the development of chemicalcompounds and methods for their application as plant bioregulators toenhance one or more constituents of the treated plant. For example, U.S.Pat. No. 3,671,219 discloses a process for increasing the sucrose yieldof sugarcane by treating sugarcane a few weeks prior to harvest with aquaternary ammonium salt which is a benzyl dimethyl alkyl or substitutedalkyl ammonium halide. U.S. Pat. No. 3,833,350 describes a method ofinducing carotenoid synthesis or accumulation in plants, fruits, andvegetables, by treating the plants just before or after harvest with ahalogenated phenoxytriethylamine or halogenated phenylthiotriethylamine.U.S. Pat. Nos. 3,684,530; 3,864,501; 3,911,148, and 3,911,152 disclosemethods for increasing the carotenoid pigment of fruits and vegetablesby treating the surface of harvested fruits or vegetables with compoundsincluding substituted 2-(p-diethylaminoethyloxybenzal) acetone or(substituted phenoxy) trialkylamines.

U.S. Pat. Nos. 4,204,859 and 4,322,242 describe a method for increasingrubber hydrocarbons in guayule and Hevea rubber plants by application ofcertain substituted phenoxytrialkylamines to 4 or 8-month old plants.U.S. Pat. No. 4,159,903 discloses a method for increasing polyisopreneproduction in rubber producing plants such as guayule by application ofsubstituted trialkylamines. U.S. Pat. No. 4,363,188 describes a methodof stimulating the in vitro propagation of polyisoprene containingplants from a nutrient medium by the addition of certain substitutedtrialkyl amines to the medium.

U.S. Pat. No. 4,797,153 discloses a method for increasing total plantbiomass and individual plant constituents such as protein, lipid, sugar,and essentials oils by application of certain substitutedphenoxytrialkylamines and substituted phenylthiotrialkyl amines orakalkylmorpholium halides. The compounds are applied in bioregulatoryamounts to plants at an early state of plant development, for example,to seeds, plant seedlings, or plant buds, or to trees during flower budswell.

U.S. Pat. Nos. 5,298,483; 5,304,529, and 5,324,707 describe methods forenhancing plant growth by treating plants at an early stage of plantdevelopment with a bioregulatory amount of one or more (benzylsubstituted) trialkylamine ether compounds. The enhanced plant growthincludes increases in photosynthesis, total plant biomass, and plantconstituents including increases in vitamin C, carotenoids, andessential oil contents of citrus fruit.

SUMMARY OF THE INVENTION

The present invention is directed towards two new classes of novelbioactive compounds. The first class comprises 2-diethylaminoethyl!-2-methylpropyl ethers shown in Group I, below. Thesecond class comprises 2- N-methylbenzylaminoethyl! substituted ethercompounds shown in Groups II-IV, below. The compounds in all groups haveactivity as plant biochemical regulators, and when applied to plants inbioregulatory amounts, they elicit superior biological responses inplants at very low levels of concentration, including increase in totalplant biomass, increase in yield, and increase in crop quality. Inaddition, some of the novel bioactive compounds stimulate synthesis oftaxol and related taxanes in yew plants. One compound, 2-diethylaminoethyl!-2-methylpropylether causes plants treated with thecompound to have resistance to chewing insects. The compound 2-diethylaminoethyl!-2-methyl-2-phenylpropylether causes plants treatedwith the compound to have resistance to sucking insects.

The compounds of the invention may be categorized as follows:

Group I. 2- Diethylaminoethyl!-2-methylpropylethers of the structure##STR1## wherein R₁ is hydrogen, methyl or phenyl; or

(b) an acid addition salt of the compounds of (a).

Group II. 2- N-Methylbenzylaminoethyl!-2-methylpropylethers of thestructure ##STR2## wherein R₂ is hydrogen or methyl; or

(b) an acid addition salt of the compounds of (a).

Group III. 2- N-Methylbenzylaminoethyl!benzylethers of the structure##STR3## wherein R₃ and R₄ are in the mere and para positions,respectively, on the ring, and wherein R₃ is hydrogen or methyl and R₄is methyl, or wherein R₃ and R₄ are both chlorine; or

(b) an acid addition salt of the compounds of (a).

Group IV. 2- N-Methylbenzylaminoethyl!-2-methyl-2-phenylpropylether ofthe structure ##STR4##

(b) an acid addition salt of the compound of (a).

In one aspect of the invention the compounds are used as plantbioregulator compounds for enhancing plant growth including increasingtotal plant biomass and important plant constituents thereby increasingcrop yield and plant quality. The compounds are applied in effectivebioregulatory amounts, this is, an amount sufficient to increase totalplant biomass but insufficient to inhibit plant growth. Application iscarried out at an early stage of plant development, that is, to the seedor to a plant or plant part during the active cell division stage ofplant development. It has been found that the application of thecompounds of the invention causes the treated plants to form and storevaluable plant constituents over that of untreated plants. Thus plantswhich have been treated with the bioregulatory compounds of theinvention have greater total biomass than untreated plants resulting inincreased agricultural crop production per unit area. Moreover,increases in photosynthesis and increases in important plantconstituents such as protein, lipid, sugar, carotenoid content, plantwaxes and essential oil content are observed in treated plants thatproduce the same, compared to untreated control plants. Pigmentaccumulation in plant leaves and fruits is increased. Increases in seedand flower yields have also been observed.

Further, enhanced plant growth is demonstrated by increases in totalsoluble solids, vitamin or nutrient contents of fruits harvested fromtreated plants compared to untreated controls.

In most cases the invention increases the growth rate of the treatedplant relative to untreated plants, resulting in accelerated maturation.Shorter growing periods effect a decrease in the labor and cost ofproduction and effect a decrease in the use of energy sources such asfossil fuel which are used in fertilizer production. Moreover,accelerated and increased growth make likely the possibility thatgrowing cycles will be shorter while yielding a harvest equivalent orsuperior to that of untreated plants. Such a harvest would be greatersince the treated plants exhibit increased biomass. It is evenconceivable that multiple harvests can be achieved within growingseasons. These possibilities offer promise for increased foodproductions at reduced costs to alleviate food shortages throughout theworld.

Another aspect of the invention is application of selected compounds toincrease the content of taxol and related taxanes in yew plants.

Another aspect of the present invention is application of selectedcompounds to elicit resistance in plants to sucking or chewing insects.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows the visible spectra of extracts of anthocyanin pigmentsfrom Red Flame seedless grapes treated with the compound of theinvention, 2- N-methylbenzylaminoethyl!-2-methylpropylether (NBIA), theprior art bioregulators DCPTA and MBTA, and control. The y-axis isoptical density (O.D.). The x-axis is wavelength (λ) in rim. Theabsorption maximum (λ_(max)) for each curve is at 518 nm.

FIG. 2 shows the effect of the compound 2-N-methylbenzylaminoethyl!-2-methylpropylether (NBIA) on the yew (Taxusspp.) plant. The treated plant is on the left and the control plant ison the right.

FIGS. 3 shows the effect of the compound 2-diethylaminoethyl!-2-methylpropylether (IBTA) in eliciting resistance inplants to chewing insects. The control plant is on the left and thetreated plant is on the right.

DETAILED DESCRIPTION OF THE INVENTION

In one aspect of the invention, the compounds of the invention are plantbiochemical regulators. The compounds effect plant biomass developmentand plant constituent formation. In most cases, earlier crop maturationis observed. The compounds significantly increase plant biomass, cropyield, and yield quality. Pigment accumulation in plant leaves andmature fruits is increased. The bioregulatory benefits of the inventionare obtained by applying any of the compounds of the invention in aneffective bioregulatory amount to plants at an early stage of plantdevelopment such as to plants seeds, plant seedlings, plant buds orimmature fruits.

Without any intention of limiting the scope of the invention, it istheorized that the compounds used in the method of the invention play arole in the photosynthetic pathway in green plants. It is theorized thatapplication of the compounds to the developing green plant causesincreased fixation of carbon dioxide in the photosynthetic pathwaythereby increasing the carbon atoms available for synthesis of totalbiomass and individual plant constituents. It is further theorized thatuse of the compounds at an early stage of plant or fruit development andbefore completion of cell differentiation manipulates the geneticexpression of the plant so as to tap unused biological potential. Thusas new cells develop under the influence of the bioregulatory compounds,they possess increased capacity to form and store valuable materials andto form increased amount of plant tissues. The combination of enhancedphotosynthate supply and enhanced photosynthate utilization appears tomaintain positive and balanced correlations between crop yield and yieldquality. No negative imbalances appear to be observed.

Examples, by way of illustration and not limitation, of compounds of theinvention are:

Group I. 2- Diethylaminoethyl!-2-methyl-2-substituted propyl etherswherein the 2-substituent is hydrogen, phenyl or methyl.

Group II. 2- N-Methylbenzylaminoethyl!-2-methyl-2-substituted propylethers wherein the 2-substitutent is hydrogen or methyl.

Group III. 2- N-Methylbenzylaminoethyl! substituted benzyl etherswherein the substituents are in the meta and para positions,respectively, on the phenyl ring, and wherein the meta substituent ishydrogen or methyl and the para substituent is methyl, or wherein themeta and para substituents are both chlorine.

Group IV. 2- N-Methylbenzylaminoethyl!-2-methyl-2-phenylpropyl ether.

The invention also encompasses the acid addition salts of the compoundsof the invention.

The ether compounds of the invention are prepared using commerciallyavailable starting materials. The appropriate alcohol is refluxed withsodium metal to yield the sodium alkoxide. The appropriate substitutedalkyl chloro or bromo halide is added to the sodium alkoxide, and themixture is refluxed to obtain the ether compound of the invention. Thesodium halide byproduct is removed by filtration or other means known inthe art. Acid addition salts of the ether are readily produced by theaddition of an acid, for example, hydrochloric acid, as is known in theart.

The synthesis of the ethers of the invention is illustrated as follows:##STR5## wherein X is chloride or bromide; wherein R is:

Group I: (C₂ H₅)₂ N--

Groups II-IV: ##STR6## wherein R' is:

Group I: --C(CH₃)₂ R₁

Group II: --C(CH₃)₂ R₂ ##STR7## wherein R₁, R₂, R₃ and R₄ are as definedabove.

Exemplary of the synthesis of the compounds of the invention is thesynthesis of 2- N-methylbenzylaminoethyl!-2-methylpropylether, which isdescribed in detail in Example 1, below.

The acid addition product is conveniently prepared by adding acid to theether as known to those in the art.

Purification of the free amine is conveniently carried out by vacuumdistillation. Purification of the acid addition salt is convenientlycarried out by crystallization.

To obtain plant bioregulator effects, the compounds are applied duringthe active cell division stage of plant development. Only oneapplication is needed for effecting plant responses. We have found thatabout 3-4 weeks after application even trace amounts of the bioregulatorof the invention cannot be detected in the plant tissues. Thebioregulator disappears, yet the effects are already established in theyoung plant cells. Application at the active cell division stage is thecritical feature for transmittal of the bioinduced regulatory geneexpression information from one cell to another. Treatment protocolsinclude seed treatment and foliar application at the early seedlingstage of growth, that is, shortly after germination and seedlingemergence and during stages of active cell division of the plant, forexample, at the 2-4 true leaf stage. Responses are drastically reducedwhen foliar application is made after active cell division has ceasedand application made during cell elongation stage. The foregoingtreatment protocols are especially useful for annual crops includingdicots and monocots and floral plants and ornamentals. Exemplary dicotsare tomato, radish, sugarbeet, and cotton. Exemplary monocots are wheat,corn, barley, oats, and grasses.

For vine-grown crops, application is made during stages of activedevelopment of the shoots, preferably shortly after shoot emergence.Treatment at a later stage of berry set results in minimal responses.For example, on deciduous fruit vines such as grapes, application shouldbe made shortly after shoot emergence (2-5 cm); applications at time ofberry blossom/berry set are too late.

For tree-grown crops, application is made during the early stages ofactive development of the fruit, for example, during flower bud swell orshortly after the opening of the bud. Conveniently, application may bemade a week before or after flower bud swell. For citrus trees,application can be made at the flower bud swell as described above;application can also be made a week before or during fruit developmentwhen the fruit cells are in the active cell division stage and beforematurity into the cell elongation stage, that is, when the fruits arenot more than about 0.5-1.5 cm in diameter. On nondeciduous fruit treessuch as citrus, it is preferred that application be made at blossom timeor no later than shortly after fruit set. On deciduous fruit trees suchas peaches, apricots, and nectarines, it is preferred that applicationbe made at blossom time or no later than at fruit set and emergence ofshoots/leaves.

On floral plants such as pansy, petunia, geranium, and carnation,applications are carried out at early seedling stage (3-5 leaf stages)or seed soak (3-8 hours, depending on ease of solution uptake). Forother floral plants such as tulips, the bulbs can be soaked overnightprior to cold treatment/conditioning and planting.

For vegetatively propagated plants like sugarcane, or shrubs such asCandelilla, application should be made at the developmental growthstages equivalent to the ones aforementioned.

To obtain plant bioregulator effects, the compounds of the invention areapplied in an effective bioregulator amount, that is, an amounteffective to increase plant biomass but insufficient to inhibit growthof the plant.

The compounds of the invention have activity at low concentration.Treatment is conveniently applied by seed treatment or foliarapplication. Treatment rates are about 0.0125 to 10 parts per million(ppm).

Generally, where the compounds are applied to the seeds, theconcentration is about 0.001 to 0.01 mg of active ingredient per seed.Application is conveniently made by dissolving the compound or the acidsalt in water with a water-wetting agent solution (0.05 to 0.1% ofwetting agent) at a concentration of 0.01 to 10 ppm in the diluent andsoaking the seeds for 3 to 8 hours. Other means of treatment of seedssuch as encapsulation of the seeds with the compounds by conventionalmethods are encompassed by the invention.

On transplanting of seedlings, root soak techniques may be employed.Generally the roots of the seedlings are soaked in about 0.1 to 10 ppmof the bioregulator solution from about 5-30 minutes. Soaking time in aparticular instance is determined by ease in which the bioregulator istaken up by the roots. The seedlings are transplanted after root soakwithout drying.

When foliar application is made to the seedling at the 2-4 leaf stage,the treatment is about 0.001 to 0.1 mg active ingredient per plant. Thiscan be accomplished by using a treatment rate of about 0.0125 to 10 ppm.The plants are sprayed until drip-off. The specific amount in aparticular instance depends on several factors such as size of theplant, how broad the leaves are, type of plant, e.g., monocot or dicot.Generally 10-15 ml of the treatment solution is sufficient.

Appropriate wetting agents and penetrating agents such aspolyoxyethylene (20) sorbitan monooleate (Tween 80) and Kinetic™, anonionic wetter/spreader/penetrant/adjuvant proprietory blend ofpolyalkyleneoxide modified polydimethylsiloxane and organosilicanesurfactants! (Helena Chemical Company, Phoenix, Ariz.) as known in theart may be added to aid in plant treatment.

As stated above, the compounds of the invention when applied inaccordance with the method of the invention, substantially increasetotal biomass, enhance the amount of some or all plant constituents andin many cases increase the rate of growth in green plants over untreatedplants as long as constituents such as water and light which arenecessary for plant growth are present in the required amount. Forexample, increases in photosynthesis and increases in important plantconstituents such as protein, lipid, sugar, carotenoid content, plantwaxes and essential oil content are observed in treated plants thatproduce the same, compared to untreated control plants. Pigmentaccumulation in plant leaves and fruits is increased. Increases in seedand flower yields have also been observed. Further, enhanced plantgrowth is demonstrated by increases in total soluble solids, vitamin ornutrient contents of fruits harvested from treated plants compared tountreated controls. In most cases the invention increases the growthrate of the treated plant relative to untreated plants, resulting inaccelerated maturation.

It has been found that in studies conducted wherein the compounds werecompared with the bioregulator compounds disclosed in U.S. Pat. No.4,797,153, specifically 3,4-dichlorophenoxytriethylamine (2-diethylaminoethyl!-3,4-dichlorophenylether) (DCPTA) and the bioregulatorcompound disclosed in U.S. Pat. No. 5,298,483, specifically 2-diethylaminoethyl!-4-methylbenzylether(N,N-diethylaminoethyl(4-methylbenzyl)ether) (MBTA), it was determinedthat compounds of the present invention are generally more effective asplant bioregulators than the bioregulator compounds disclosed in the'153 or '483 patents. For example, as shown in Example 4, below,application of the novel bioactive compounds at 1 ppm increased biomassin radish plants 28 to 98% compared to plants treated with DCPTA, andincreased biomass 21 to 97% compared to MBTA. The superior nature of thenew compounds is observed in the comparison of increases of fresh radishroot weight ranging from 17% to 193% when compared to DCPTA at the 1 ppmconcentration and 18% and 194% when compared to MBTA. The novelbioactive compound, 2- N-methylbenzylaminoethyl!-4-methylbenzylether atthe low level of 0.1 ppm increased biomass and root weight by 86% and177% compared to untreated controls. In contrast, DCPTA and MBTA wereineffective at the 0.1 ppm level.

The superior performance of the compounds of the invention over DCPTAand MBTA is also illustrated in FIG. 1 (see Example 10 below), andExamples 12-14, below. Thus, the compounds of the invention exhibit astructure-activity correlation superior to the disclosed prior art andthus represent an advance in the state of the art of bioregulators.

Selected novel bioactive compounds of the invention increase the contentof taxol and related taxanes in yew plants including Taxus baccatta,Taxus brevifolia, T. sp. x T. media cv. Hicksii, and Taxus cuspidata.The compounds are Group I compound wherein R₁ is hydrogen; Group IIcompound where R₂ is hydrogen; Group III compounds, particularlyN-methyl-2-benzylaminoethyl-4-methylbenzylether and3,4-dimethylbenzylether and 3,4-dichlorobenzylether analogs; or acidaddition salts of the foregoing compounds

The compounds are applied in effective amounts, that is, an amountsufficient to increase taxol and related taxanes but insufficient toinhibit growth of the yew plant. Related taxanes include taxolprecursors, e.g., 3,10-deacetylbaccattin-III and taxol analogs, e.g.,baccattin-III.

Application is carried out at an early stage of plant development, thatis, to the seed or to a plant seedling, or plant part (clone). Thecompounds have activity at low concentration. Treatment is convenientlyapplied by seed treatment, seedling root soak or foliar application.Treatment rates are about 1 to 10 ppm.

One useful technique employed is to treat roots of seedlings propagatedfrom clones (cuttings). Seedlings are treated by soaking roots in thebioregulator solution such as 1, 5, 10 ppm with a wetting agent, e.g.,0.1% Kinetic™ for 10 to 20 minutes and transplanting without drying.Seed treatment is carried out by soaking seeds in the bioregulatorsolution (1 to 10 ppm) with a wetting agent, e.g., 0.1% Kinetic™.

As shown in Example 16, below, application of the novel bioactivecompounds increased taxol content in yew plants 112 to 175% andincreased biomass by 33 to 41% compared to control plants. Increases of25 to 27% taxol content and 10 to 15% biomass were observed in yewplants treated with the novel bioactive compounds compared to plantstreated with DCPTA. These increases in taxol were observed throughoutthe above ground portion of the plant, e.g., stems, branches, andneedles.

This application provides an important means of enhancing the productionof the important anticancer drug taxol from natural sources.

Selected compounds are useful to elicit resistance in plants to suckingor chewing insects. The compound 2-diethylaminoethyl!-2-methylpropylether causes plants treated with thecompound to have resistance to chewing insects. The compound 2-diethylaminoethyl!-2-methyl-2-phenylpropylether causes plants treatedwith the compound to have resistance to sucking insects. Surprisingly,while the compounds in themselves do not have pesticidal properties,they elicit resistance in plants to insects.

Examples of chewing insects are cabbage looper, tobacco horn worm, andpotato beetle. Examples of sucking insects are aphids, sweet potatowhitefly, and silverleaf whitefly.

The compounds are applied in effective resistance-eliciting amounts,that is, an amount sufficient to cause resistance by the plant to theselected insect, but insufficient to inhibit growth of the plant. Seedsoak rather than foliar treatment is the preferred treatment. Seed soakaffords immediate protection to emerging seedlings whereas foliartreatment exposes young seedlings to insect damage before treatmenttakes effect. For example, tomato seeds are soaked in the bioregulatorsolution at a concentration of about 1 to 10 ppm in a wetting agent,e.g., 0.1% Kinetic™ for 6-8 hours. Treated seeds are planted withoutdrying.

This application is illustrated in Examples 17 and 18, below.

EXAMPLES

The following examples are intended only to further illustrate theinvention and are not intended to limit the scope of the invention whichis defined by the claims.

Example 1

This example describes the synthesis of the compounds of the invention.Exemplary is the synthesis of 2-N-methylbenzylaminoethyl!-2-methylpropylether.

One hundred grams of N-methyl-N-benzylethanolamine were added to 14grams of sodium in toluene and refluxed with gentle stirring for about 3hours or until all the sodium had reacted or dissolved. To this reactionmixture were slowly added 84 grams of isobutylbromide in 100 ml toluene.The whole reaction mixture was refluxed with gentle stirring for anadditional 6 hours and allowed to cool to room temperature. Theprecipitated sodium bromide was removed by filtration. The filtrate waswashed three times with equal volumes of water, and then the tolueneremoved using a rotary evaporator. The residue was taken up in 200 mldiethylether, and the solution was cooled in an ice bath. One hundredgrams of ice were added to the cooled solution. Five hundred ml of 20 %HCl (previously cooled in an ice bath) were added to the reactionproduct and stirred 1 hour. The diethylether was allowed to evaporate atroom temperature. The residue was taken up in 100 ml isopropyl alcoholand placed in an ice bath or cold room for crystallization.Recrystallization two times yielded 80 grams of product.

The acid addition product was prepared by adding hydrochloride acid tothe ether product with stirring. Purification was carded out byrecrystallization.

Example 2

This example sets forth the structures and ¹³ CNMR data for six of thecompounds of the invention. The ¹³ CNMR data were determined on thehydrochloric acid addition salts of the compounds in D₂ O using aJEOL-270 spectrometer in the FT mode, 60 min., concentration: 50 mg/2ml.

Group I

2- Diethylaminoethyl!-2-methylpropylether (IBTA). ¹³ CNMR (67.8 MHz, D₂O) 8.6, 18.9, 27.8, 48.0, 48.3, 51.5, 64.5. ##STR8##

2- Diethylaminoethyl!-2-methyl-2-phenylpropylether (PBTA). ¹³ CNMR (67.8MHz, D20) 8.7, 20.7, 24.2, 40.6, 48.6, 55.0, 67.2, 129.1, 130.0, 130.6,131.4. ##STR9## Group II

2- N-Methylbenzylaminoethyl!-2-methylpropylether (NBIA). ¹³ CNMR (67.8MHz, D₂ O) 20.7, 29.7, 42.5, 56.7, 62.2, 66.1, 80.2, 131.1,131.6, 132.4,133.1. ##STR10## Group III

2- N-Methylbenzylaminoethyl!-4-methylbenzylether (NBMA). ¹³ CNMR (67.8MHz, D₂ O) 20.2, 41.6, 54.4, 62.6, 64.2, 79.2, 130.1, 130.2, 130.8,131.2, 131.8, 132.2, 133.2, 133.6. 2-N-Methylbenzylaminoethyl!-4-methylbenzylether in the hydrochloride form(water soluble) is extremely hygroscopic and must be stored with adesiccant. The crystalline material must be handled under dryatmospheric conditions. ##STR11##

2- N-Methylbenzylaminoethyl!-3,4-dimethylbenzylether (NBDA). ¹³ CNMR(67.8 MHz, D₂ O) 20.2, 21.6, 41.5, 52.1, 62.8, 63.2, 79.1, 130.6, 130.7,130.9, 131.1, 131.2, 131.2, 132.6, 133.1, 133.2, 133.6. ##STR12## GroupIV

2- N-Methylbenzylaminoethyl!-2-methyl-2-phenylpropylether (NBPA). ¹³CNMR (67.8 MHz, D₂ O) 20.1, 24.6, 42.5, 56.7, 62.1, 66.1, 80.1, 129.1,129.6, 130.8, 131.2, 131.7, 131.7, 132.1, 132.6. ##STR13##

Example 3

This example describes the plant bioregulator effects of a compound ofthe invention using two different wetting agents. Solutions of thehydrochloric acid salt of 2- diethylaminoethyl!-2-methylpropylether (10ppm active ingredient) in 0.1% wetting agent in water were preparedusing polyoxyethylene (20) sorbitan monooleate (Tween 80 from SigmaChemicals) or Kinetic™ (proprietory blend of polyalkyleneoxide modifiedpolydimethylsiloxane and organosilicane surfactants from Helena ChemicalCompany, Phoenix, Ariz.). The bioregulator solutions were applied totable radish Raphanus sativus cv. Champion! at the 2-3 leaf state tofoliage runoff. Control plants were treated the same as the test plantsexcept that no bioregulator compound was used. The solution applied tocontrol plants was 0.1% wetting agent. Six replicates of the test andcontrol plants were carried out for each wetting agent. The plants wereharvested 31 days after planting, and the biomass fresh weight (gm)! ofeach plant was measured.

Results. The effect of the plant bioregulator compound of the inventionon radish biomass using different wetting agents is shown in Table 1. Inboth cases, biomass was increased significantly over the control.However, even though uniform wetting was observed with both wettingagents, increased biomass amounts were obtained using bioregulator inKinetic™ compared to bioregulator in Tween 80.

                  TABLE 1                                                         ______________________________________                                        Radish Biomass Fresh Weight (gm)                                              Kinetic ™          Tween 80                                                Compound.sup.1                                                                          Control 2   Compound.sup.1                                                                          Control 2                                     ______________________________________                                        50.6      21.4        34.5      22.8                                          50.4      23.1        32.7      19.7                                          51.0      19.7        33.3      21.1                                          51.2      22.4        31.3      18.4                                          50.1      18.8        32.2      20.7                                          49.1      23.9        32.6      19.3                                          ______________________________________                                         .sup.1 10 ppm 2 diethylaminoethyl2-methylpropylether in 0.1% wetting          agent.                                                                        .sup.2 0.1% wetting agent.                                               

Example 4

This example describes bioregulator effects of the compounds of theinvention on radish plants.

The hydrochloric acid salts of the following compounds were prepared asdescribed above:

2- diethylaminoethyl!-2-methylpropylether (IBTA);

2- diethylaminoethyl!-2-methyl-2-phenylpropylether (PBTA);

2- N-methylbenzylaminoethyl!-2-methylpropylether (NBIA);

2- N-methylbenzylaminoethyl!-4-methylbenzylether (NBMA);

2- N-methylbenzylaminoethyl!-3,4-dimethylbenzylether (NBDA);

2- N-methylbenzylaminoethyl!-2-methyl-2-phenylpropylether (NBPA).

Aqueous solutions containing the bioregulator acid salts (10, 1, or 0.1ppm active ingredient) and 0.1% Kinetic™ were prepared. The bioregulatorsolutions were applied in a single application per treatment to tableradish Raphanus sativus cv. Red Devil B! at early seedling (2-3 leaf)stage to foliage runoff (10 ml/plant) as a foliar application. Forpurposes of comparison, applications of known bioregulators, 2-diethylaminoethyl!-3,4-dichlorophenylether (DCPTA) and 2-diethylaminoethyl!-4-methylbenzylether (MBTA), were carried out asdescribed above. Control plants were treated as described above using0.1% Kinetic™ wetting agent and no bioregulator.

The plants were grown in 1 gallon pots in the greenhouse. Six replicatesof the test treatments, comparison treatments, and controls were carriedout. The experimental pots were arranged randomly.

The plants were observed during the growing period to assess differencesbetween the test treatments, comparison treatments, and controls. Theplants were harvested 32 days after planting.

The wet (fresh) weight yields of total biomass (whole plant) and rootswere measured. To obtain the root weight, the roots were separated fromthe leaves and stems and weighed without prior drying, i.e., wetweights. The anthocyanin pigment content of the plants was determined asfollows: taproots were freeze-dried, weighed, and extracted withmethanol. Absorbance readings were taken on the spectrophotometer at 520nm and correlated to amount.

Results. Increase in green color of the leaves of the test radish plantsover the control plants and plants treated with comparison bioregulatorswas noticeable within a week after application of the compounds of theinvention and comparison bioregulators, reflecting an increase in thechlorophyll content. The test radishes attained a deeper red colorationthan the controls and plants treated with comparison bioregulators,indicating an increase in the anthocyanin pigment content. The foliageof the test plants was somewhat larger and more upright at a steeperangle than the controls.

As seen in Table 2, application of the compounds of the inventionincreased biomass root weight and anthocyanin pigment content (color)over the controls and comparison bioregulators. Overall, the increasesin biomass exhibited by the new compounds ranged from 19% (1.2-fold) to93% (1.9-fold) compared to control plants. Several of the novelbioactive compounds (IBTA, PBTA, NBMA) were most effective at 1 ppm andincreased biomass ranging from 36% (1.4-fold) for PBTA to 93% (1.9-fold)for NBMA when compared to control plants; also NBMA increased biomass86% (1.8-fold) at the even lower concentration level of 0.1 ppm. BothDCPTA and MBTA were completely ineffective at 0.1 ppm level. At the 10ppm level, biomass increases ranged from 23% (1.2-fold) for NBPA to 56%(1.6-fold) for NBIA compared to control plants.

All of the novel bioactive compounds exhibited superior properties overeither DCPTA or MBTA. At the 1 ppm concentration level, biomassincreases ranged from 21% (1.2-fold) for NBPA to 98% (2-fold) for NBMAwhen compared to DCPTA and 21% (1.2-fold) to 97% (2-fold) when comparedto MBTA. At the 10 ppm, biomass increases ranged from 10% for NBPA to41% for NBIA when compared to DCPTA and 7% for NBPA to 37% for NBIA.

Overall, increases in fresh root weight shown by the novel bioactivecompounds ranged from 14% for NBIA to 183% for NBMA when compared to thecontrols and these results were observed at the 1 ppm concentrationlevel; even at the lower level of 0.1 ppm NBMA showed a 177% increase inroot weight. At the 10 ppm concentration level, increases in root weightranged from 36% for NBPA to 73% for IBTA when compared to controlplants.

The superior nature of the new compounds is observed in the comparisonof increases of fresh radish root weight ranging from 17% for NBIA to193% for NBMA when compared to DCPTA at the 1 ppm concentration and 18%and 194%, respectively, when compared to MBTA. Again, both DCPTA andMBTA were completely ineffective at the 0.1 ppm level. At the 10 ppmlevel, fresh root increases ranged from 23.6% (1.2-fold) for NBPA to57.1% (1.6-fold) for IBTA when compared to DCPTA and 15.0% (1.2-fold) to46.2% (1.5-fold) increases respectively on comparison with MBTA.

Also as seen in Table 2, application of the compounds of the inventionproduced anthocyanin pigment content increases ranging from 43% to 104%compared to the control, 47% to 108% compared to DCPTA at the 1 ppmconcentration, and 28% to 81% compared to MBTA at the 1 ppmconcentration.

In sum, the activity at the low levels of 1 ppm and 0.1 ppm are uniqueto the compounds of the invention, in contrast to known plantbioregulators such as DCPTA and MBTA. Neither DCPTA nor MBTA producedresponses greater than the control at 1 ppm. Some increases with DCPTAand MBTA over the control were observed at 10 ppm, but these were lessthan those with the compounds of the invention. The greatest increaseswere observed for 2- N-methylbenzylaminoethyl!-4-methylbenzylether(NBMA).

                  TABLE 2                                                         ______________________________________                                        Radish Plants                                                                 Treatment  Biomass    Root      Anthocyanin                                   Compound                                                                              ppm    Wet Wt (gm)                                                                              Wet Wt (gm)                                                                           Root: dry wt μg/g                        ______________________________________                                        IBTA    10     55.4 ± 3.3                                                                            25.3 ± 1.8                                       IBTA    1      57.7 ± 4.7                                                                            25.2 ± 2.3                                                                         6154                                        PBTA    10     49.5 ± 2.6                                                                            20.1 ± 2.4                                       PBTA    1      51.1 ± 3.5                                                                            18.9 ± 2.0                                                                         5987                                        NBIA    10     59.0 ± 4.6                                                                            23.9 ± 1.5                                       NBIA    1      54.0 ± 3.5                                                                            16.5 ± 1.3                                                                         6872                                        NBMA    1      72.9 ± 2.9                                                                            41.3 ± 4.0                                                                         7698                                        NBMA    0.1    70.2 ± 2.6                                                                            40.4 ± 2.8                                                                         7714                                        NBDA    10     57.5 ± 2.9                                                                            22.9 ± 1.1                                       NBDA    1      48.4 ± 2.9                                                                            18.7 ± 1.6                                                                         5431                                        NBPA    10     46.1 ± 2.7                                                                            19.9 ± 1.8                                       NBPA    1      44.7 ± 2.4                                                                            18.9 ± 1.4                                                                         5612                                        DCPTA.sup.1                                                                           10     41.8 ± 3.1                                                                            16.1 ± 1.1                                       DCPTA.sup.1                                                                           1      36.9 ± 3.4                                                                            14.1 ± 1.9                                                                         3697                                        MBTA.sup.1                                                                            10     43.1 ± 2.1                                                                            17.3 ± 1.6                                       MBTA.sup.1                                                                            1      37.1 ± 2.6                                                                            13.9 ± 1.8                                                                         4254                                        Control 0      37.7 ± 2.8                                                                            14.6 ± 1.2                                                                         3786                                        ______________________________________                                         .sup.1 Not in accordance with the invention. For comparison purposes only                                                                              

Example 5

This example describes bioregulator effects of the compounds of theinvention on tomato plants.

Solutions of the hydrochloric acid salts of compounds IBTA, PBTA, NBIA,NBMA, NBDA, and NBPA containing 0.1% Kinetic™ nonionic wetting agentwere prepared. Treatment rates were 10, 1, or 0.1 ppm active ingredient.Foliar application of the solutions were applied in a single applicationper treatment to young tomato Lycopersicum esculentum cv. Pixie!seedlings at the early seedling (3-4 true leaf) stage by thoroughlydrenching with the solutions until run off (approx. 10 mlsolution/plant). Control plants were treated the same as the test plantsexcept that no bioregulator compound was used. The solution applied tocontrol plants was 0.1% Kinetic™. The plants were grown in thegreenhouse in 2 gallon pots. The seeds were planted Mar. 26, 1993 andthe fruits were harvested Jun. 21, 1993.

In another test, the bioregulator solutions were applied to tomatoseeds. The seeds were soaked for 6 hours in solutions containing 0.1%Kinetic™. Treatment rates were 10, 1, or 0.1 ppm active ingredient. Theseeds were planted after soaking and without prior drying. The plantswere grown in the greenhouse in 2 gallon pots.

In both tests, the plants were observed for bioregulator effects. Fruityield, fruit size, percent ripe fruit and yield per plants weremeasured. Determinations of Brix percent were made on fully ripe fruit.Brix was determined by a hand-held battery-operated digitalrefractometer already correlated to read Brix. Carotenoid content wasdetermined on fully ripe fruit grown from treated seedlings by the usualmethod of taking a reading at 450 mμ of the extracted pigment solutionin hexane using a spectrophotometer (Yokoyama et at., Proceedings of theInternational Society of Citriculture 3:717-722, (1977)). The resultsrepresent six replicate plants.

Results. Bioregulator activity of the compounds of the invention at lowlevels of concentration was observed. No residue of the bioregulatorswas detectable by HPLC after 2-3 weeks of application in the plant leafor in the fruit which developed about 2-3 months later.

Table 3 shows the effects of the bioregulators on fruit quality andyield of tomato plants grown from treated seedlings. Significantincreases in soluble solids content over control plants, as reflected inthe Brix percentage results, were observed, accompanied by increases incarotenoid content. Due to the latter increase, improved coloration,particularly in the flesh was seen in the fruits of thebioregulator-treated plants when compared to those of the untreatedplants.

Responses appeared to be more uniform and consistent in the treatedplants and greater variations were usually observed in the untreatedcontrol plants. The fruits of the treated plants matured earlier andwere more uniform, and the desirable tomato flavor was more pronounced.The overall quality of the fruit appeared to be vastly improved. Therewas an increased yield of fruits due in part to increased branching andnumber of flowers. The fruits were usually larger. Balanced plantperformances were observed without any negative imbalances. As shown inTable 4, similar results were observed on seed treatment.

                                      TABLE 3                                     __________________________________________________________________________    Tomato Plants                                                                 Treatment                                                                            Brix Carotenoids                                                                         Fruit                                                       Cmp ppm                                                                              %    μg/g fresh wt                                                                    total/plant                                                                        size g/fruit                                                                       % ripe                                                                            yield kg/plant                                __________________________________________________________________________    IBTA                                                                              10 8.2 ± .04                                                                       186 ± 7                                                                          40   41   90  1.6                                           IBTA                                                                              1  7.9 ± .04                                                                       158 ± 4                                                                          35   39   88  1.4                                           PBTA                                                                              10 8.0 ± .04                                                                       182 ± 8                                                                          34   39   82  1.3                                           PBTA                                                                              1  6.0 ± .05                                                                       168 ± 6                                                                          40   36   78  1.5                                           NBIA                                                                              10 7.0 ± .03                                                                       160 ± 8                                                                          46   37   74  1.7                                           NBIA                                                                              1  7.2 ± .04                                                                       156 ± 9                                                                          46   37   72  1.7                                           NBMA                                                                              1  8.4 ± .04                                                                       191 ± 8                                                                          47   39   92  1.8                                           NBMA                                                                              0.1                                                                              7.3 ± .04                                                                       172 ± 7                                                                          38   40   89  1.5                                           NBDA                                                                              10 6.2 ± .07                                                                       152 ± 7                                                                          39   36   84  1.4                                           NBDA                                                                              1  6.4 ± .03                                                                       158 ± 6                                                                          40   35   77  1.4                                           NBDA                                                                              0.1                                                                              6.5 ± .04                                                                       150 ± 8                                                                          43   31   78  1.3                                           NBPA                                                                              10 5.8 ± .05                                                                       145 ± 7                                                                          38   28   71  1.1                                           NBPA                                                                              1  5.5 ± .06                                                                       137 ± 8                                                                          34   26   66  0.9                                           Contl                                                                             0  5.1 ± .04                                                                        78 ± 8                                                                          32   24   31  0.8                                           __________________________________________________________________________

                  TABLE 4                                                         ______________________________________                                        Tomato Plants                                                                             Fruit                                                             Treatment                                                                              Brix                       yield                                     Cmp   ppm    %        total/plant                                                                          size g/fruit                                                                         % ripe                                                                              kg/plant                            ______________________________________                                        IBTA  10     7.4 ± .04                                                                           38     39     89    1.5                                 IBTA  1      7.1 ± .05                                                                           31     36     85    1.4                                 PBTA  10     7.6 ± .06                                                                           32     35     84    1.1                                 PBTA  1      6.9 ± .03                                                                           39     37     80    1.4                                 NBIA  10     6.7 ± .05                                                                           37     41     79    1.6                                 NBIA  1      7.1 ± .05                                                                           41     40     82    1.7                                 NBMA  1      7.7 ± .06                                                                           47     39     83    1.8                                 NBMA  0.1    7.2 ± .04                                                                           41     36     81    1.5                                 NBDA  10     6.5 ± .07                                                                           36     32     83    1.3                                 NBDA  1      6.7 ± .06                                                                           37     31     84    1.4                                 Contl 0      5.2 ± .04                                                                           31     25     30    0.8                                 ______________________________________                                    

Example 6

The bioregulator effects of the compounds of the invention on spinachwere determined. Foliar application of solutions of the hydrochloricacid salts of compounds IBTA, NBIA, NBMA, and NBDA (10 or 1 ppm activeingredient) with 0.1% Kinetic™ wetting agent were applied in a singleapplication per treatment to spinach Spinacea oleracea cv. New Zealand!at early seedling (2-3 leaf) stage to foliage runoff (approximately 20ml/plant). Control plants were treated the same as the test plantsexcept that no bioregulator compound was used. The solution applied tocontrol plants was 0.1% Kinetic™.

The plants were grown in the greenhouse in 2 gallon pots and harvested60 days after planting. Eight replicates were carried out. Biomass(whole plant) and chlorophyll (lead values were determined. Chlorophyllcontent was determined by the usual method of spectrophotometricreadings.

Results. The results are tabulated in Table 5. Biomass was increasedsignificantly over control plants. Total chlorophyll content wasincreased. The leaves appeared to be greener in coloration (reflectingthe increase in the total chlorophyll content) and larger and moreupright at a sharper angle.

                  TABLE 5                                                         ______________________________________                                        Spinach                                                                                                     Chlorophyll                                     Treatment           Biomass   total                                           Compound  ppm       dry wt gm mg/g fresh wt                                   ______________________________________                                        IBTA      10        10.07 ± .31                                                                          1.98 ± .11                                   NBIA      10        10.21 ± .39                                                                          1.82 ± 1.2                                   NBMA      1         10.59 ± .43                                                                          1.69 ± .15                                   NBDA      10        10.10 ± .42                                                                          1.58 ± .14                                   Control   0          5.76 ± .65                                                                          1.28 ± .17                                   ______________________________________                                    

Example 7

The bioregulator effects of the compounds of the invention on barleywere determined. Foliar application of solutions of the hydrochloricacid salts of compounds IBTA, PBTA, NBIA, NBMA, NBDA, and NBPA (10, 1,or 0.1 ppm active ingredient) containing 0.1% of Kinetic™ nonionicwetting agent were applied to foliage runoff (approximately 10 ml/plant)in a single application to robust barley (Hordeum vulgare L. cv. Robust)at early seedling stage shortly after germination (when the plants wereabout 6-10 cm tall). Control plants were treated the same as the testplants except that no bioregulator compound was used. The solutionapplied to control plants was 0.1% Kinetic™.

The plants were grown in the greenhouse, five plants per 1 gallon pot;six replicate pots per treatment. Plants were harvested at about 3months. Bioregulator effects on the plants were observed.

Determinations of biomass and kernel weight were made. Kernel weight wasdetermined as follows. Dry kernels separated from the spikes werecollected for each of the barley plants, and weighed.

Results. Positive bioregulator responses were observed. The leaves ofthe treated plants were broader and longer, resulting, it is believed,in more efficient photosynthesis. As shown in Table 6, bioregulatortreatment significantly increased the biomass weight and kernel weightcompared to the control. Increases in kernel weight were a result ofincreases in the number of kernels per treated plant, that is, therewere more kernels per "spike."

                  TABLE 6                                                         ______________________________________                                        Barley                                                                        Treatment      Biomass       Kernels                                          Bioregulator                                                                              ppm    dry wt grm    dry wt grams                                 ______________________________________                                        IBTA        10     41.9 ± 2.1 12.6 ± .9                                 IBTA        1      52.7 ± 1.0 17.2 ± .8                                 PBTA        10     41.5 ± 0.8 12.9 ± .9                                 PBTA        1      38.5 ± 1.8 10.5 ± .5                                 NBIA        10     51.1 ± 1.3 17.1 ± .7                                 NBIA        1      52.6 ± 2.3 12.1 ± .9                                 NBIA        0.1    47.1 ± 2.3 13.8 ± .5                                 NBMA        10     52.1 ± 3.7 13.6 ± 1.0                                NBMA        1      55.0 ± 2.5 15.5 ± .9                                 NBMA        0.1    56.6 ± 2.3 16.2 ± .8                                 NBDA        10     44.1 ± 2.6 12.9 ± .8                                 NBDA        1      46.5 ± 3.2 13.7 ± .9                                 NBPA        10     37.6 ± 3.9 11.1 ± .8                                 NBPA        1      35.7 ± 3.4 10.5 ± 1.0                                Control     0      14.7 ± 0.8  6.2 ± .3                                 ______________________________________                                    

Example 8

The bioregulator effects of the compounds of the invention on corn (Zeamays L.) were determined. Solutions of the hydrochloric acid salts ofthe compounds IBTA, NBIA, NBMA, and NBDA at treatment rates of 10, 1, or0.1 ppm active ingredient with 0.1% Kinetic™ nonionic wetting agent wereapplied in a single application as foliar applications to runoff(approximately 10 ml/plant) to corn cv. Early Xtra-Sweet hybrid! at theearly seedling stage shortly after germination when the plants wereabout 6-8 cm tall. Control plants were treated the same as the testplants except that no bioregulator compound was used. The solutionapplied to control plants was 0.1% Kinetic™.

The plants were grown in the greenhouse in 2 gallon pots; eightreplicates per treatment, and harvested 2 months after planting. Theplants were observed to assess differences between treated and controlplants. Biomass was determined. The biomass results given in Table 7represent only the stem (stalk) and leaf; roots are not included. At thestage of maturity of the corn plant when the biomass analysis wascarried out, the corn had not fully matured, thus no corn cob and kernelweights are given.

Results. Biomass was increased significantly over control plants Gable7). Additionally, in all of the numerous experiments conducted, thetassels always appeared before the silks, assuring good pollination forseed formation. This is valuable because one of the problems in the cornindustry is poor pollination due to the silk appearing prior to tasselappearance, thus resulting in reduced seed formation and production.Further, the leaf structure was altered somewhat in that the leaf waslonger and broader, having an impact on photosynthesis. Again, theunusual feature of the new bioregulators of the invention, particularlythe compound 2- N-methylbenzylaminoethyl!-4-methylbenzylether (NBMA), istheir effectiveness at the extremely low concentration levels.

                  TABLE 7                                                         ______________________________________                                        Corn                                                                          Treatment          Biomass                                                    Compound        ppm    dry wt (gm)                                            ______________________________________                                        IBTA            10     57.9 ± 3.4                                          IBTA            1      72.5 ± 2.3                                          NBIA            10     58.8 ± 3.1                                          NBIA            1      63.3 ± 2.3                                          NBMA            1      52.6 ± 2.5                                          NBMA            0.1    53.4 ± 1.5                                          NBDA            10     44.4 ± 2.1                                          NBDA            1      45.6 ± 1.3                                          Control         0      30.1 ± 3.4                                          ______________________________________                                    

Example 9

This example describes the bioregulator effects of the compounds of theinvention on wheat (Triticum aestivum durum L.). Solutions of thehydrochloric acid salts of compounds IBTA, NBPA, NBIA, NBMA, and NBDA(10, 1, or 0.1 ppm active ingredient) containing 0.1% Kinetic™ nonionicwetting agent were applied in a single application as foliar applicationto runoff (approximately 10 ml/plant) to durum wheat at early seedlingstage (4-6 cm tall). Control plants were treated the same as the testplants except that no bioregulator compound was used. The solutionapplied to control plants was 0.1% Kinetic™. The plants were grown in 2gallon pots in the greenhouse, eight replicates per treatment and eightreplicates for the control. The plants were harvested 2 months afterplanting. The yields of biomass (dry weight) and kernels (dry weight)were measured. The results are tabulated in Table 8.

In another test, the bioregulator solutions of IBTA, PBTA, NBIA, NBMA,and NBDA were applied to wheat seeds as a seed soak. Durum wheat seedswere soaked for 6 hours in the bioregulator solutions (10, 1, or 0.1 ppmactive ingredient) containing 0.1% Kinetic™, and planted directlywithout drying. The plants were grown in 2 gallon pots in thegreenhouse, 8 replicates. The plants were harvested 2 months afterplanting. Yields of biomass and kernels were measured. The results aretabulated in Table 9.

Results. The leaves of the treated plants were longer and broader. Thetotal number of kernels per plant was increased significantly,indicative of yield increase response. As shown in Tables 8 and 9,application of the bioregulators of the invention significantlyincreased biomass and kernel weight compared to the controls.

                  TABLE 8                                                         ______________________________________                                        Wheat                                                                         Treatment            Biomass   Kernels                                        Compound  ppm        dry wt (gm)                                                                             dry wt (gm)                                    ______________________________________                                        IBTA      10         24.09 ± 1.23                                                                          9.97 ± 0.25                                IBTA      1          34.56 ± 1.94                                                                         11.84 ± 0.64                                NBPA      10         30.03 ± 2.82                                                                          9.94 ± 0.53                                NBPA      1          34.92 ± 1.27                                                                         11.39 ± 0.58                                NBIA      10         37.13 ± 2.88                                                                         12.15 ± 0.32                                NBIA      1          40.40 ± 1.84                                                                         14.22 ± 0.50                                NBIA      0.1        43.55 ± 1.57                                                                         15.21 ± 0.61                                NBMA      10         35.88 ± 3.17                                                                         11.45 ± 0.63                                NBMA      1          37.27 ± 2.10                                                                         11.69 ± 0.60                                NBDA      10         32.58 ± 2.89                                                                         11.86 ± 0.36                                NBDA      1          34.00 ± 0.89                                                                         11.91 ± 0.60                                Control   0          17.23 ± 1.32                                                                          7.54 ± 0.73                                ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        Wheat                                                                         Treatment            Biomass   Kernels                                        Compound  ppm        dry wt (gm)                                                                             dry wt (gm)                                    ______________________________________                                        IBTA      10         24.37 ± 1.46                                                                         9.75 ± 0.44                                 IBTA      1          27.02 ± 1.98                                                                         9.43 ± 0.76                                 PBTA      10         23.20 ± 1.22                                                                         6.93 ± 0.29                                 PBTA      1          28.39 ± 1.12                                                                         9.84 ± 0.61                                 NBIA      10         27.01 ± 1.04                                                                         9.40 ± 0.76                                 NBIA      1          28.41 ± 1.26                                                                         9.47 ± 0.60                                 NBIA      0.1        30.16 ± 1.12                                                                         10.18 ± 0.75                                NBMA      10         31.75 ± 1.26                                                                         8.66 ± 0.60                                 NBMA      1          30.54 ± 1.25                                                                         9.74 ± 0.63                                 NBMA      0.1        25.85 ± 0.97                                                                         8.35 ± 0.41                                 NBDA      10         27.65 ± 1.86                                                                         9.82 ± 0.85                                 NBDA      1          28.61 ± 1.58                                                                         9.19 ± 0.42                                 Control   0          15.93 ± 0.61                                                                         6.72 ± 0.28                                 ______________________________________                                    

Example 10

This example describes the bioregulator effects of the compounds of theinvention on grapes. A solution of the hydrochloric acid salt of thecompound of the invention 2-N-methylbenzylaminoethyl!-2-methylpropylether (NBIA) (10 ppm activeingredient) containing 0.1% Kinetic™ nonionic wetting agent was appliedto field-grown Red Flame seedless grape Vitis vinifera cv. Red Flame!vines grown in Coachella Valley, Calif. A single application to runoffwas made shortly after shoots appeared in early spring (shoots were at6-10 cm growth stage). For purposes of comparison, solutions of the acidsalts of known bioregulators MBTA and DCPTA (10 ppm active ingredient)in 0.1% Kinetic™ were applied to Red Flame seedless grape vines the sameas for the test bioregulator. Control plants were treated the same asthe test plants except that no bioregulator compound was used. Thesolution applied to control plants was 0.1% Kinetic™.

Twenty kg samples of the test, comparison, and control grapes wereharvested May 21, 1994, Jun. 5, 1994, and Jun. 15, 1994. The grapeberries were separated from the stems, crushed, and aliquots of thegrape juice analyzed for Brix percent. The visible spectra of waterextracts of the anthocyanin pigments of the test, comparison, andcontrol samples were obtained on a visible spectrophotometer.

Results. The application of the compound 2-N-methylbenzylaminoethyl!-2-methylpropylether on vines of the Red Flameseedless grapes resulted in improving the overall quality of theberries. As shown in Table 10, the soluble solids content as reflectedin the Brix readings was increased significantly, resulting in bettertasting fruits with improved flavor. The bioregulator of the inventionperformed much better than MBTA or DCPTA. The color was also enhanceddue to increased production of the anthocyanin pigments as shown inFIG. 1. A deeper enhanced red coloration of the berries and juices wasobserved.

                  TABLE 10                                                        ______________________________________                                        Grapes                                                                        Harvest      Brix %                                                           No.   Date       NBIA    MBTA.sup.1                                                                            DCPTA.sup.1                                                                          Control                               ______________________________________                                        1st   May 21, 1994                                                                             15.9    15.2    15.0   15.1                                  2nd   June 5, 1994                                                                             19.9    18.7    17.6   17.1                                  3rd   June 15, 1994                                                                            22.8    20.2    19.5   18.2                                  ______________________________________                                         .sup.1 Not in accordance with the invention. For comparison purposes only                                                                              

Example 11

This example describes the bioregulator effects of the compounds of theinvention on cantaloupe (Cucumis melo L. var. cantalupensis Naud.).Aqueous solutions of the hydrochloric acid salt of 2-diethylaminoethyl!-2-methylpropylether (IBTA) (10 ppm active ingredient)containing 0.1% Kinetic™ wetting agent were applied to cantaloupe seedsby making the seeds for 6 hours. The control cantaloupe seeds weresoaked with an aqueous solution of 0.1% Kinetic™ wetting agent for 6hours. The seeds were planted in 3 gallon pots and grown in thegreenhouse. After 4 months, the cantaloupes were harvested, cut in half,and observed for bioregulator effects.

Results. Treated cantaloupe showed thicker flesh and smaller seed cavitythan the control. The color of flesh of the treated melon was visiblymuch deeper colored. This deeper orange coloration was due to increasesin the carotenoid content.

Example 12

This example describes the bioregulator effects of the compounds of theinvention on petunia (Petunia hybrida Velm.) floral plants. Solutions ofthe hydrochloride acid salt of 2-N-methylbenzylaminoethyl!-4-methylbenzylether and 2-N-methylbenzylaminoethyl!-2-methylpropylether (10, 1, 0.1, and 0.0125ppm active ingredient) containing 0.1% Kinetic™ wetting agent wereapplied to petunia plants at early seedling (3-4 leaf stage) as foliarapplication until runoff (approximately 10 ml/plant). For comparisonpurposes solutions of DCPTA and MBTA (10, 1, 0.1, and 0.0125 ppm activeingredient) in 0.1% Kinetic™ were applied to petunia floral plants. Thecontrols were seedlings treated with an aqueous solution of 0.1%Kinetic™ wetting agent. The plants were grown in 1 gal pots, 6replicates. Greenhouse protocols called for the experimental pots to bearranged randomly on the table. Photos were taken when flowers startedto appear and at or near full bloom.

Results. The petunia plant responses were visibly observed for responsesand photos taken of the results. Positive bioregulator responses wereobserved at a level of concentration as low as 0.0125 ppm. Strikingincreases in anthocyanin color were visibly observed compared to thecontrol. Neither DCPTA nor MBTA produced significant responses at thelow level of 1 ppm and produced none at 0.1 or 0.0125 ppm. Reduced levelof responses of DCPTA and MBTA were observed at 10 ppm when compared tothe bioregulators of the invention at the same level of concentration.The foliage of the plants treated with the compounds of the inventionwas somewhat larger and more upright at a steeper angle than thecontrols.

Example 13

This example describes the bioregulator effects of the compounds of theinvention on pansy (Viola tricolor hortensis) plants. Solutions ofhydrochloric salt of 2- N!-methylbenzylaminoethyl!-2-methylpropyletherand 2- N-methylbenzylaminoethyl!-4-methylbenzylether (0.0125, 0.1, 1, 10ppm) with 0.1% Kinetic^(TM) were applied as foliar applications to pansyseedlings (3-4 leaf stage). For comparison purposes, solutions of DCPTAand MBTA (0.0125, 0.1, 1, and 10 ppm) in 0.1% Kinetic™ were applied topansy seedlings. Control seedlings were treated with aqueous solutionsof 0.1% Kinetic™. The seedlings were grown in 1 gal pots, with 6replicates.

Results. Similar responses to petunia floral plants were observed withpansies. Increases in anthocyanin coloration were observed visiblycompared to the controls. Again, neither DCPTA or MBTA producedsignificant responses at the low level of 1 ppm and none at all at 0.1or 0.0125 ppm as compared to the bioregulator compounds of the inventionat the same concentration. The foliage of the plants treated with thecompounds of the invention attained a deeper green coloration,indicative of increased accumulation of chlorophylls. The leaves weresomewhat larger and broader.

Example 14

Mature (11 year old) citrus trees of Olinda Valencia orange (Citrussinensis (L.) Osbeck) located at the Agricultural Experiment Station,University of California, Riverside, Calif. were used to test theeffects of the compounds of the invention on citrus. Each treatmentgroup contained four trees. The treatment groups consisted of thehydrochloric acid salts of the following: DCPTA -50 ppm; MBTA -50 ppm;2- N-methylbenzylaminoethyl!-2-methylpropylether (NBIA) -50 ppm; 2-N-methylbenzylaminoethyl!-4-methylbenzylether (NBMA) -50 ppm. Allsolutions contained 0.1% Kinetic™ wetting agent. Control plants weretreated the same as the test plants except that no bioregulator compoundwas used. Only a single application was made of each treatment. Fourliters of a solution was applied to each tree to cover the entirefoliage canopy shortly after fruit set. Fruit sizes ranged from 0.5 to1.5 cm in fruit diameter. Randomly selected canopy mature fruits fromfour replicate trees were combined for fruit quality analysis. Foranalysis 10 fruits were selected from each treatment group. Total freshfruit weight was determined. Peel thickness was determined on fruits cutin half. Fruits were juiced using an electric hand-juicer fitted with a3 mm screen. The final juice volume and juice fresh weight weredetermined. Peel fresh weight after juicing and pulp fresh weight weredetermined. Juice samples were centrifuged at 25,000 xg for 15 minutes.The supernatant decanted and serum total soluble solids were determinedusing a hand-held battery-operated digital refractometer alreadycorrected to Brix values. Vitamin C content was determined using a2,6-dichloroindophenol titrimetric method of the Association of OfficialAnalytical Chemists, 15th ed., 1990, Arlington, Va., 96721. Peel wasseparated from the endocarp (4 fruits) and freeze-dried. The carotenoiddetermination was carried out according to the usual method (H. Yokoyamaet at., Proceedings of the International Society of Citriculture3:717-722, (1977)).

Results. The results are presented in Tables 11 and 12. As shown inTable 11, significant increases in the fruit size were obtained usingthe compounds of the invention. In contrast, fruit treated with DCPTAand MBTA remained comparable to controls. The application of thecompounds of the invention also caused increases in juice yield asreflected in ml juice per fresh fruit weight compared to the controls orto DCPTA or MBTA. The nutritional value of the fruit was enhanced asreflected in the increases in the vitamin C content of 33.3% for NBIAand 31.9% for NBMA over that of controls. The soluble solids increased,as shown in the Brix readings, of 39.6% for NBIA and 37.7% for NBMA overthat of control. Peel thickness decreased by 14.3% for NBIA and 16.3%for NBMA, indicating an increase in the fruit endocarp, thus increase inthe juice content.

On citrus fruits, NBIA and NBMA proved again to be superior performingcompounds and outperformed both MBTA and DCPTA in providing morenutritious, higher soluble content and juicier fruits with thinnerpeels. For both NBIA and NBMA, juice yield increases of 8.2% over DCPTAand 6.0% over MBTA were observed. For NBIA, increases in vitamin Ccontent of 22.4% over DCPTA and 15.4% over MBTA were observed; for NBMA,increases in vitamin C were 21.1% over DCPTA and 14.2% over MBTA. ForNBIA, increases in soluble solids content, as reflected in Brixreadings, were 20.3% over DCPTA and 16.5% over MBTA; for NBMA 18.7% overDCPTA and 15.0% over MBTA. Desirable thinner peels were observed forNBIA and NBMA: for NBIA, decreases in peel thickness of 10.9% over DCPTAand 6.8% over MBTA were observed, and for NBMA, decreases in peelthickness of 8.7% over DCPTA and 4.5% over MBTA were observed.

                                      TABLE 11                                    __________________________________________________________________________    Citrus                                                                        Fruit    ml Juice/g       Percent of Fruit                                    Treatment                                                                          Diam                                                                              fruit                                                                              Vitamin C                                                                          Serum                                                                             Peel                                                                             juice                                                                             peel + pulp                                     50 ppm                                                                             mm  fresh wt                                                                           mg/100 ml                                                                          Brix                                                                              mm fresh wt                                                                          fresh wt                                        __________________________________________________________________________    NBIA 65.4 a.sup.1                                                                      0.53 a                                                                             56.8 a                                                                             14.8 a                                                                            4.1 b                                                                            51.9 a                                                                            46.9 a                                          NBMA 65.2 a                                                                            0.53 a                                                                             56.2 a                                                                             14.6 a                                                                            4.2 b                                                                            51.8 a                                                                            46.7 a                                          DCPTA.sup.2                                                                        64.1 b                                                                            0.49 b                                                                             46.4 b                                                                             12.3 a                                                                            4.6 b                                                                            51.4 a                                                                            47.1 b                                          MBTA.sup.2                                                                         64.0 b                                                                            0.50 b                                                                             49.2 b                                                                             12.7 a                                                                            4.4 b                                                                            51.5 a                                                                            47.1 b                                          Control                                                                            63.9 b                                                                            0.49 b                                                                             42.6 c                                                                             10.6 b                                                                            4.9 a                                                                            50.7 b                                                                            47.4 b                                          __________________________________________________________________________     .sup.1 Means associated with the same letter are not significantly            different, according to Duncan's multiple range tests  P >5%!.                .sup.2 Not in accordance with the invention. For comparison purposes only                                                                              

Visual observations indicated that both endocarp and flavedo of treatedfruits exhibit enhanced coloration with NBIA and NBMA showing somewhatdeeper enhancement. These observations are confirmed in Table 12. As canbe seen from the data, increased pigmentation was observed in both peeland endocarp on application of NBIA and NBMA. In the endocarp, NBIA andNBMA increased the carotenoid content 71% and 44%, respectively, overthe controls. Again, both NBIA and NBMA proved superior to either DCPTAor MBTA. NBIA increased carotenoid content 53 % over DCPTA and 22% overMBTA. NBMA increased carotenoid content 43% over DCPTA and 20% overMBTA. In the peel, NBIA increased carotenoid content by 62% and NBMA by41% over controls. Increased carotenoid contents were observed for NBIAof 62% and for NBMA of 41% over the controls. On comparison with DCPTAand MBTA, NBIA showed increases of 47% over DCPTA and 44% over MBTA;NBMA showed increases of 28 % over DCPTA and 25 % over MBTA.

                  TABLE 12                                                        ______________________________________                                                      Carotenoid                                                                    Content (μg/g dry wt)                                        Treatment       Endocarp Peel                                                 ______________________________________                                        NBIA            266      302                                                  NBMA            224      263                                                  DCPTA.sup.1     174      205                                                  MBTA.sup.1      186      210                                                  Control         156      186                                                  ______________________________________                                         .sup.1 Not in accordance with the invention. For comparison purposes only                                                                              

Example 15

A large candelilla plant (Euphorbia antisiphylitica Zucc.) was selectedfrom Teralingua, Tex., and cuttings were grown in the greenhouse at theUniversity of California at Riverside. After one year of growth, thesecuttings were treated with the novel plant bioregulators at severallevels of concentration. The wetting agent used was Kinetic™ at 0.1%w/v.

Six months after treatment the stems were harvested. At harvest time thestems were cut 2 cm. above ground and extracted with chloroform for 5min. three times. The combined extracts and the extracted stems weredried and weighed and the yield of the raw wax expressed as apercentage; dry wt wax g/dry tissue stems g.

Results. As shown in Table 13, significant increases in wax yield at the1.0 and 10 ppm levels were observed in Candelilla plants treated with 2-N-methylbenzylaminoethyl!-2-methylpropylether (NBIA). Significantincrease in wax yield was observed at the lower level of concentration0.05 ppm in plants treated with 2-N-methylbenzylaminoethyl!-4-methylbenzylether (NBMA).

                  TABLE 13                                                        ______________________________________                                        Treatment      Concentration ppm                                                                           Wax Yield %.sup.1                                ______________________________________                                        Control 0.1% Kinetic ™                                                                    0             2.83 a                                           NBIA           0.1           3.01 ab                                          NBIA           1.0           3.37 bc                                          NBIA           10.0          3.50 c                                           NBMA           0.05          3.57 c                                           NBMA           1.0           2.76 a                                           ______________________________________                                         .sup.1 Duncan's Multiple Range Test was used to separate the means.      

Example 16

This example describes the effects of the compounds of the invention onyew plants. Aqueous solutions of the hydrochloric acid salts of 2-diethylaminoethyl!-2-methylpropylether (IBTA) and 2-N-methylbenzylaminoethyl!-2-methylpropylether (NBIA) having 10 and 1 ppmactive ingredient and containing 0.1% Tween 80 wetting agent wereprepared. For purposes of comparison, solutions of 10 and 1 ppm DCPTAcontaining 0.1% Tween 80 wetting agent were prepared. The controlsolution contained only 0.1% Tween 80 wetting agent. Roots of rootedcuttings of yew plants Taxus brevifolia and T. sp. x media cv. Hicksiiwere soaked for 20 minutes in the test, comparison, and controlsolutions before transplanting. The plants were grown in 2 gallon potsoutdoors under a sunscreen in Pasadena, Calif. Shortly after theappearance of new growth, the test plants were treated with 1 ppm activeingredient foliar application until runoff. Controls were treated withthe control solution until runoff. The plants were harvested 40 weeksafter the initial treatment. Yields of biomass and taxol content weredetermined. Biomass yield was determined as the average dry weight ofwhole plants including needles; 4 plants. Taxol content was determinedas the average taxol content of stems of whole plants stripped ofneedles; 4 plants. Taxol content was determined by the method of N.Vidensek et al.,(N. Videnesek, P. Lee, A. Campbell, and C. Carlson, J.Natural Products 53:1609-1610 (1990)).

Results. The compounds of the invention significantly increased theyields of biomass and taxol content compared to DCPTA-treated plants orthe control. Increases over the control ranged from 112% to 175%increases in taxol content and 33% to 41% increases in biomass. Theresults are tabulated in Table 14.

                  TABLE 14                                                        ______________________________________                                        Yew Plants                                                                    Taxol Content       Biomass                                                   (% dry wt.)         (gm dry wt)                                                                T. sp. x media     T. sp. x media                            Treatment                                                                            T. brevifolia                                                                           cv Hicksii T. brevifolia                                                                         cv Hicksii                                ______________________________________                                        IBTA   0.017 ± .001                                                                         0.009 ± .001                                                                          56.8 ± 2.3                                                                         41.7 ± 1.7                             NBIA   0.021 ± .001                                                                         0.011 ± .001                                                                          60.1 ± 2.4                                                                         43.9 ± 2.2                             DCPTA.sup.1                                                                          0.011 ± .001                                                                         0.005 ± .001                                                                          47.3 ± 2.6                                                                         35.7 ± 2.2                             Control                                                                              0.008 ± .001                                                                         0.004 ± .002                                                                          42.8 ± 2.3                                                                         31. 1± 1.6                             ______________________________________                                         .sup.1 Not in accordance with the invention. For comparison purposes only                                                                              

The yew plant (Taxus baccatta) was treated with an aqueous solution ofthe hydrochloric acid salt of 2-N-methylbenzylaminoethyl!-2-methylpropylether (NBIA) (10 ppm) as aseedling root soak (15 rain) prior to transplanting. The wetting agentwas 0.1% Kinetic™. The control plant was treated with a solution of 0.1%Kinetic™.

Results. As shown in FIG. 2, the yew plant treated with the novelbioactive compound of the invention (on the right in the figure) showedsignificantly greater biomass compared to the control plant (on theleft).

Example 17

This example describes the effects of selected compounds of theinvention on plants treated with the compounds and exposed to suckinginsects.

Tomato seeds were soaked for 6 hours in aqueous solutions of thehydrochloric acid salt of 2-diethylaminoethyl!-2-methyl-2-phenylpropylether (PBTA) or 2-diethylaminoethyl!-2-methylpropylether (IBTA) (10 ppm active ingredient)containing 0.05% Tween 80 wetting agent. Control seeds were treated with0.05% Tween 80. Seeds were planted Jul. 15, 1992 and grown in thegreenhouse. After germination, the test and control plants were exposedto continuous populations of the silverleaf whitely Bemisia argentifoliiBellows and Perring! which is a "sucking insect" from Jul. 29, 1992.Plants were harvested Sep. 2, 1992. Each treatment had ninereplications.

Results. Plants treated with 2-diethylaminoethyl!-2-methyl-2-phenylpropylether showed resistance to thesilverleaf whitely (sucking insect), whereas plants treated with 2-diethylaminoethyl!-2-methylpropylether did not. The results are shown inTable 15. The leaf area index (LAI) data gives an indication in relativenumber of nymphs reduced by treatment of plants. The addition of aphenyl group to the isobutyl moiety is the structural difference betweenthe two compounds. These results were totally unexpected. No anti-insectproperties were observed in previous experiments with DCPTA or MBTA.

                  TABLE 15                                                        ______________________________________                                        Tomato Plants                                                                 Treatment           B. argentifolii                                                                            Nymphs                                       Compound  ppm       per leaf     LAI.sup.1 × 1000                       ______________________________________                                        IBTA      10        134.7 ns     18.5 ab.sup.2                                PBTA      10        107.6        15.5 b                                       Control    0        120.7        21.6 ab                                      ______________________________________                                         .sup.1 LAI = leaf area index measured in cm.sup.2 by a LiCOr.sup.R            Portable Area Meter.                                                          .sup.2 Means associated with the same letter are not significantly            different (P <0.05).                                                     

Example 18

This example describes the effects of 2-diethylaminoethyl!-2-methylpropylether on plants treated with thecompound and exposed to chewing insects.

Young seedlings of cantaloupes (Cucumis melo L. var. cantalupensisNaud.), cabbages (Brassica oleracea L.), and cucumbers (Cucumis sativusL.) were treated with 2- diethylaminoethyl!-2-methylpropylether (IBTA)by foliage application to runoff of an aqueous solution of thehydrochloric acid salt of IBTA (10 ppm active ingredient) containing a0.1% Kinetic™ wetting agent. Control plants were seedlings treated withan aqueous solution of 0.1% Kinetic™ wetting agent. The treated andcontrol plants were grown outdoors and there was a heavy infestation ofchewing insects.

Results. All the leaves of the control plants were heavily damaged bythe chewing insects whereas the leaves of the treated plants remainedvirtually undamaged. FIG. 3 shows the effects of IBTA on cantaloupeplants 30 days after foliar application. As can be seen in the figure,significant insect damage occurred on the control plant (on the left inthe figure), whereas virtually no damage occurred on the treated plant(on the right). As discussed above, this compound had no effect againstsucking insects. No anti-insect properties were observed in previousexperiments with DCPTA or MBTA.

What is claimed is:
 1. A compound selected from the group having thestructure ##STR14## wherein R₂ is methyl; and (b) an acid addition saltthereof.
 2. A compound selected from the group having the structure##STR15## wherein R₃ and R₄ are in the meta and para positions,respectively, on the ring, and wherein R₃ is methyl and R₄ is hydrogenor methyl, or wherein R₃ and R₄ are both chlorine; and(b) an acidaddition salt thereof.
 3. The compound of claim 2 wherein R₃ is methyland R₄ is hydrogen.
 4. The compound of claim 2 wherein R₃ and R₄ aremethyl.
 5. A compound selected from the group having the structure##STR16## and (b) an acid addition salt thereof.
 6. A method forenhancing plant growth, comprising applying to a plant a compoundselected from the group consisting of: ##STR17## wherein R₁ is phenyl;##STR18## wherein R₂ is hydrogen or methyl; ##STR19## wherein R₃ and R₄are in the meta and para positions, respectively, on the ting, andwherein R₃ is hydrogen or methyl find R₄ is methyl, or wherein R₃ and R₄are both chlorine; ##STR20## (e) an acid addition salt of compounds(a)-(d); said compound being applied to the plant immediately prior toor at a time when cell differentiation and growth of the plant or flowerbuds are great, that is, to seeds, to plant seedlings, or to treesduring flower bud initiation, bud swell or during a period ofexponential vegetative growth, said compound being applied to the plantin an effective bioregulatory amount, this is, an amount sufficient toenhance plant growth but insufficient to inhibit plant growth, saidenhancing of plant growth consisting of an increase in total plantbiomass and plant constituents selected from the group consisting ofprotein, lipid, sugar, and essential oil.
 7. The method of claim 6wherein the enhancing of plant growth further consists of an acceleratedstructural maturation of the plant and reduction of days to crop harvestcompared to an untreated plant.
 8. The method of claim 6 wherein theenhancing of plant growth further consists of an increase in plantconstituents selected from the group consisting of pigment, solublesolids, vitamin content, and juice content.
 9. The method of claim 6wherein the compound is 2-diethylaminoethyl!-2-methyl-2-phenylpropylether, 2-N-methylbenzylaminoethyl!-2-methylpropylether, 2-N-methylbenzylaminoethyl!-4-methylbenzylether, 2-N-methylbenzylaminoethyl!-3,4-dimethylbenzylether, 2-N-methylbenzylaminoethyl!-2-methyl-2-phenylpropylether, or acid additionsalt thereof.
 10. The method of claim 6 wherein the plant is a dicot.11. The method of claim 6 wherein the plant is a monocot.
 12. The methodof claim 6 wherein the plant is a floral plant.
 13. A method ofincreasing the content of taxol in a yew plant, comprising applying to ayew plant a compound selected from the group consisting of 2-N-methylbenzylaminoethyl!-4-methylbenzylether,N-methyl-2-benzylaminoethyl-4-methylbenzylether, 2-N-methylbenzylaminoethyl!-3,4-dimethylbenzylether, 2-N-methylbenzylaminoethyl!-3,4-dichlorobenzylether, or acid addition saltthereof, said compound being applied to the plant at an early stage ofplant development, that is, to the seed, to a plant seedling or plantpart, said compound being applied to the plant in an amount effective toincrease taxol in the plant compared to an untreated yew plant.
 14. Amethod of causing a plant to become resistant to sucking insects,comprising applying to a plant 2-diethylaminoethyl!-2-methyl-2-phenylpropylether or acid addition saltthereof, said compound being applied to the plant in an amount effectiveto cause the plant to become resistant to sucking insects compared to anuntreated plant.